| Improved “cure on demand” of aromatic bismaleimide with thiol triggered by retro-Diels-Alder reaction |
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| 引用本文： | Vincent Froidevaux,Melanie Decostanzi,Abdelatif Manseri,Sylvain Caillol,Bernard Boutevin,Remi Auvergne. Improved “cure on demand” of aromatic bismaleimide with thiol triggered by retro-Diels-Alder reaction[J]. Frontiers of Chemical Science and Engineering, 2021, 15(2): 330-339. DOI: 10.1007/s11705-020-1929-6 |
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| 作者姓名： | Vincent Froidevaux Melanie Decostanzi Abdelatif Manseri Sylvain Caillol Bernard Boutevin Remi Auvergne |
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| 作者单位： | Institut Charles Gerhardt Montpellier |
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| 基金项目： | The authors thank the Hutchinson Company for its financial support,Biobased Polymer Company for reactants supply. |
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| 摘 要： | This study focuses on the synthesis of new liquid aromatic bismaleimide monomers in order to improve self-curing on demand(SCOD)systems previously based on aliphatic bismaleimides.These SCOD systems are based on Diels-Alder(DA)/retro-DA reactions.The syntheses of new different aromatic bismaleimides with ester and amide bonds are presented.These maleimides have been protected using DA reaction and characterized by 1H NMR analysis to determine protection rate and diastereomer ratios.The retro-DA reactions of both aromatic and aliphatic DA adducts in presence of thiol molecules were studied.Kinetic analysis was monitored by 1H NMR and compared to model study.Finally,both aromatic and aliphatic bismaleimides-based polymers were synthesized with 2-mercaptoethyl ether and thermal properties of polymers were compared.The glass transition temperature values ranged from–20°C to 14°C and very good thermal stabilities were observed(up to 300°C).
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| 关 键 词： | thiol-ene polymerization self-curing on demand thia-michael addition Diels-Alder MALEIMIDE |
Improved “cure on demand” of aromatic bismaleimide with thiol triggered by retro-Diels-Alder reaction |
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| Vincent Froidevaux,M&#,lanie Decostanzi,Abdelatif Manseri,Sylvain Caillol,Bernard Boutevin,R&#,mi Auvergne. Improved “cure on demand” of aromatic bismaleimide with thiol triggered by retro-Diels-Alder reaction[J]. Frontiers of Chemical Science and Engineering, 2021, 15(2): 330-339. DOI: 10.1007/s11705-020-1929-6 |
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| Authors: | Vincent Froidevaux M&# lanie Decostanzi Abdelatif Manseri Sylvain Caillol Bernard Boutevin R&# mi Auvergne |
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| Affiliation: | Institut Charles Gerhardt Montpellier, UMR 5253-CNRS, Université de Montpellier, ENSCM, 34296 Montpellier Cedex 5, France |
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| Abstract: | This study focuses on the synthesis of new liquid aromatic bismaleimide monomers in order to improve self-curing on demand (SCOD) systems previously based on aliphatic bismaleimides. These SCOD systems are based on Diels-Alder (DA)/retro-DA reactions. The syntheses of new different aromatic bismaleimides with ester and amide bonds are presented. These maleimides have been protected using DA reaction and characterized by 1H NMR analysis to determine protection rate and diastereomer ratios. The retro-DA reactions of both aromatic and aliphatic DA adducts in presence of thiol molecules were studied. Kinetic analysis was monitored by 1H NMR and compared to model study. Finally, both aromatic and aliphatic bismaleimides-based polymers were synthesized with 2-mercaptoethyl ether and thermal properties of polymers were compared. The glass transition temperature values ranged from –20 °C to 14 °C and very good thermal stabilities were observed (up to 300 °C). |
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| Keywords: | thiol-ene polymerization self-curing on demand thia-michael addition Diels-Alder maleimide |
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